Fed up with model-off-duty dishevelment and street-style slavishness, 26-year-old Alice Gregory turns for inspiration to the quieter and more experienced dressers in her midst.

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A little over a year ago, I moved from downtown Manhattan to Brooklyn Heights, a leafy, cobblestoned neighborhood laden with pedigreed dogs and their well-heeled, mostly white-haired masters. That first day, when the movers had finally finished their hauling and gone on their way, I surveyed my new box-strewn studio, sighed with exhausted satisfaction, and went out for a walk. It was quiet. There were no recent NYU grads, no fixed-gear bikes, no "practice spaces." Often referred to as "America's first suburb," the neighborhood has been gentrified for more than a century. Some of the country's most famous writers have lived here—Arthur Miller, Norman Mailer, Truman Capote—alongside bankers, lawyers, doctors. This is not the Brooklyn made internationally legible by pop culture. There's nothing hip about it. Strolling the tree-lined street, I smiled at chic retirees in quilted jackets and elegant loafers. Like Roth's Nathan Zuckerman, first arriving at E. I. Lonoff's Berkshire farmhouse, I looked around and thought, "This is how I will live."

Though I'm younger than my zip code's median age by approximately half a century, I've never felt so surrounded by neighbors whose personal style I'd like to crib. It's not about their maturity, per se—though nothing catches my eye quite like a glossy pewter bob—it's the counterintuitive assertion of wealth: the stylish nonstyle. The boots are expensive, as are the bags and obviously the brownstones, but every other item is affordable: Gap sweaters, old anoraks, maybe an Agnès B. beret. The jeans are skinny but not tight; the jewelry is heirloom and modest; wrists are graced with—if anything—a plain black Swatch.

I know "postmenopausal psychiatrist" is not the look I should be aiming for at my age. And that, like Nora Ephron, I will "regret not having worn a bikini for the entire year I was twenty-six." But I can't help it. The woman I'm channeling when I get dressed in the morning does not know what a wedge sneaker or a BB cream is or maybe even that a material called "stretch denim" exists. She's the type of woman who shops at Eskandar, rebuys the same Issey Miyake purse every five years, attends gala events in a nylon windbreaker. She can afford—both financially and socially—to be underdressed.

It used to be that cool was hard to come by. It required either innate charisma or an energetic dedication to the new and the novel. But now, because of fast fashion and the Internet's power of immediate dissemination, any suburban teenager with Wi-Fi and $15 in her pocket can look like Erin Wasson. Cool is no longer categorically aspirational—cool is mass-market. When it comes to getting dressed in 2014, affluence—or, in my case, the illusion of it—begins to look like the last unattainable goal.

Caring about looking rich while making not a single life choice that would actually result in being rich is hard to justify. I am unwilling to forfeit my freelance schedule for a proper job, I don't have an entrepreneurial bone in my body, and my sense of self-worth is alarmingly disconnected from financial success, a fact I'm not proud of. Why would I, of all people, want to look like a museum-board member?

I think about this a lot. My wardrobe doesn't fool anyone I know personally or whose opinion I care about, nor do I wish it did. Like most people who write for a living, the sort of status I crave depends upon the respect of roughly 100 people, most of whom live within a mile of me and are just as unwealthy as I am.

But with money comes the freedom to be selectively ignorant, and for a person who relies on her ability to outnotice and outarticulate other people, a certain kind of obliviousness can feel like luxury. It's a false obliviousness, to be sure; the irony of flying under the radar in tastefully neutral, infinitely subtle style signifiers has always been that doing so takes a great deal of care, attention, and knowledge. The "knowledge," for instance, that a block heel is fine but a stacked heel is trendy; that a $5 pashmina bought off the street is perfectly good but cannot under any circumstances have fringe; that clownishly bright lipstick is acceptable but even a trace of mascara is not. While on an AARP member this uniform is successfully invisible, on a young person it's a quiet but judgmental attack on the ubiquitous "model-off-duty" uniform: the leather leggings, the acid-washed jacket, the pierced tragus.

I'm not alone in my embrace of aggressive tastefulness, nor in my turning away from underage style icons. Mary-Kate and Ashley Olsen cast not a single model under age 39 for The Row's prefall 2014 lookbook. Sporting the brand's rounded sunglasses and a dead-simple clutch coat, silver-haired skin-care entrepreneur Linda Rodin, age 65, could not cut a more enviable figure. The era of luxe, anonymous austerity that emerged in fashion circa 2010 comes courtesy of Phoebe Philo's first collection for Céline and is also indebted, to some degree, to the return of '90s-inspired minimalism first pioneered at Calvin Klein: These days, textured neutrals have replaced color; conservative, architectural cuts are de rigueur.

What lends minimalist dressing its gravitas is its price: It can't be imitated on the cheap, at least not easily. Undergrads may wear oxford shirts and brogues to class and look cleaner than they have in years, but they don't look rich and they don't look trend averse. With my entire annual net income, I could probably afford a single Céline outfit (minus the purse), but I know how to dress to defy my tax bracket. I've spent years on eBay ferreting out collections' least trendy items—camel coats, straight-legged trousers, hardware-free handbags.

I grew up comfortably upper-middle-class, but in rural Northern California, where billionaires dress like off-duty park rangers and most people drive Subarus, no matter their income. High-end mountain bikes are as flashy as you're going to get. I've never been anywhere in America that is less self-conscious about money. For this I am eternally grateful. To have one's youth sullied by an awareness of status symbols strikes me as genuinely tragic.

But though I grew up oblivious to the signifiers of wealth, I've always been hypersensitive to that egalitarian sin known as "tackiness." This was ingrained in me early on by my mother, who regularly declared things tacky: bikinis on children, cheddar cheese cut into cubes, manicures, not eating "square meals," mixing gold and silver jewelry, tennis shoes that aren't white, wet hair in public…. To be fair, it was her own mother who got her started. I'll never forget sitting on my grandparents' living room floor, reading a book and absentmindedly wrapping a bracelet around my ankle. My grandmother turned to my mother: "Tell Alice to remove that. It makes her look like a whore." I was seven.

I took these matriarchal strictures to heart, and while I rebelled in various ways, I can say with confidence that I was never tacky. By high school I had winnowed down my mother's list of acceptable clothing options even further, appending my own, more personalized prohibitions: no polka dots, no peplums, no pink. (If you have long blond hair and do not want to look feebleminded, these are all advisable injunctions.)

The self-imposed edicts served me well when I got to college and immediately fell in with a group of kids from New York City and Los Angeles who did things like intern in Paris and go to Nobu "for a snack." They were scions of companies I'd actually heard of, the close blood relatives of famous artists. They dined regularly with media moguls, rock stars, politicians. Somehow, at 18, I looked enough the part to blend in. My absorption felt inevitable and obvious, and it happened with a great deal of passivity on my part—a fact I took for granted at the time but that bewilders me in retrospect.

My previous veto on tackiness was now fortified with class-consciousness worthy of an Edith Wharton antiheroine. Though certain instances of opulence made me balk—the luxury SUVs, the exaggerated disdain for cafeteria food—I happily studied their ways. I gleaned the power of expensive androgyny: that a truly great piece—an illegal scarf made from the chin hair of Tibetan antelope, a down coat from Loro Piana—can be worn and appreciated by men and women alike. That if circumstances prevent you from eating the very best food, you might as well eat at McDonald's. That intergenerational socializing is shorthand for status. I wouldn't forsake these subdued intimidation tactics for any sum of money. The sense of entitlement I gained is arguably the most valuable thing I got out of college.

If you are young and urban dwelling, it is nearly impossible not to dress like a hipster. You can be free of bangs, tattoos, and bird-print blouses and still fall victim. Everything collapses into the detested rubric, even antithetical things: thick black glasses and wire-rimmed glasses, V-necks and crew necks, asymmetrical leather purses and promotional tote bags. American Apparel carries almost exclusively "normal" items—plain anoraks, straight-legged corduroys, polo shirts—thereby making even the most traditional outfits cool.

So what is a woman to do? It wasn't until I moved to my new ambulance-scored, diabetic-friendly neighborhood that I figured out a way to assimilate my lifetime stance against tackiness, my college-era snobbishness, and my adult desire to be taken seriously into a single uniform. My jeans are Lycra free and from the Gap. I own 15 black turtlenecks, each purchased at Uniqlo for $9.99, and I switch between a pair of Tod's black ankle boots and a pair of Stuart Weitzman over-the-knee boots—rich-mom brands, both. My winter coat is made of Gore-Tex, my bag an unremarkable leather satchel. It's thanks to my new, advanced-age neighbors (all of whom wear more or less this same thing) that I realized the trick to appearing both rich and smart is to feign ignorance. Look like a person who has no idea what's going on but employs a very good personal assistant who does. It's harder than it seems.